Matt Kester

With picturesque oak trees creating a canopy above you, Oakland is a rare gem in Orange County. Founded in 1887, Oakland is one of the oldest municipalities in Orange County. At one time, Oakland was known for being a major city of commerce (it even had a large Opera House!). This small town has what you would describe as a classic Florida “laidback lifestyle”. Located on the West Orange Trail, all the benefits of Winter Garden are only ten minutes away while you are nestled in a quieter suburb making it a perfect fit for many families in Orange County. 

Wherever you go in Oakland – you are surrounded by large trees, ensuring almost every home has mature landscaping and a deep charm. One of the most popular communities in Oakland is the new Oakland Park. This David Weekly community has beautiful new construction homes with a classic southern feel and loads of community amenities. In addition you will find countless beautiful farm style homes on large lots with plenty of room for you and your family. Some homes even have stunning views of Lake Apopka. 

Enjoy biking down the West Orange Trail on a Saturday morning, or find a perfect spot to explore in the nature preserve – regardless of where you go, I know you will appreciate this thriving small town under majestic oak trees.